For every trade acquisition like Joe Carter, Josh Donaldson and Jose Bautista, the Blue Jays have made deals that didn’t quite work out in their favor.

Shrewd moves have brought the Toronto Blue Jays to the top of the baseball world before.

The acquisition of Joe Carter and Roberto Alomar paved the way to back-to-back World Series titles. They signed aging veterans like Jack Morris, Dave Winfield, and Paul Molitor who were chasing one final shot at glory in their careers.

Josh Donaldson turned into an American League MVP in Toronto. They also got Jose Bautista in a deal for a player who later became a bullpen catcher.

But not every move has turned out in the Blue Jays’ favor. For every franchise-changing trade, free-agent signing, or front office shuffle, there have been some head-scratching decisions in the club’s 43-year history.

Here are the 10 biggest decisions the Blue Jays probably wish they had back.

DENVER, COLORADO – SEPTEMBER 18: Starting pitcher Noah Syndergaard #34 of the New York Mets throws in the first inning against the Colorado Rockies at Coors Field on September 18, 2019 in Denver, Colorado. (Photo by Matthew Stockman/Getty Images)

Blue Jays mistake No. 10: Trading Noah Syndergaard for R.A. Dickey

Knuckleballs are notoriously unpredictable. They dance, dart and dip in every possible direction. The pitch is subject to wild swings in effectiveness. Even the pitcher whose fingers release the ball has almost no control over where it ends up.

The same can be said of knuckleball pitchers, none more so than R.A. Dickey. Dickey made his Major League debut back in 2001 and moved between four teams by 2012, only once winning more than 10 games in a season. Then, in 2012 at the age of 37, he went 20-6 with a 2.73 ERA for the New York Mets, a career year that led to him winning the NL Cy Young Award.

A closer look at his numbers reveals just what an outstanding season Dickey had in 2012. He walked 2.08 batters per nine innings, a solid number for any starter but incredible for a knuckleballer. He struck out 8.9 per nine innings after only once before in his career being above six K/9, and that came nine years earlier. He was the only pitcher to throw a knuckleball that season, using the pitch 85.4 percent of the time.

The Mets had a decision to make following the season. Was Dickey’s year an aberration, or could he repeat it going forward? They decided on the former, and on Dec. 17 they shipped him to the Toronto Blue Jays in a package that included prospects Noah Syndergaard and Travis d’Arnaud.

The Blue Jays had just made a blockbuster deal with Miami for Jose Reyes, Mark Buehrle, and Josh Johnson. General Manager Alex Anthopoulos had a win-now philosophy. As promising as Syndergaard was, he was years away from playing in the Majors. Dickey was the reigning Cy Young winner who could step into the rotation right away.

Dickey remained a solid starter with the Blue Jays, winning 28 games with a 3.97 ERA in his first two seasons. He was a key part of the 2015 club that went to the ALCS and made 29 starts in 2016 but was left off the postseason roster. But he was no Syndergaard.

From 2015, the year he made his Major League debut, to 2018, Syndergaard had the fourth-lowest ERA among starting pitchers, behind only Clayton Kershaw, teammate Jacob deGrom and Max Scherzer. His average fastball velocity led all starters at 97.6 mph. And, after five years in the big leagues, he’s still just 27, more than a decade younger than Dickey was when the Blue Jays acquired him.

In four seasons in Toronto, Dickey finished with a 49-52 record and a 4.05 ERA in 130 starts. His walk rate jumped to 2.9, while his strikeouts declined to 6.6. He was good, but never again was he great like in 2012. He last pitched in the Majors in 2017. Syndergaard, meanwhile, even after Tommy John surgery earlier this year, still has many years of greatness ahead of him.

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